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Struggle Session: Emotional Affairs, Scheduled Sex, Double-Black Diamonds, and More!

Every Thursday I respond to comments, emails, DMs, and tweets from my readers and listeners. Struggle Session posts are exclusively for Magnum Subs. So, if you’re already a Magnum Sub, thank you for being my sub and read on! If you’d like to become a my sub — which gains you access to the Magnum Lovecast (more guests, more calls, no ads), the Maxi Savage Love column (more Qs, more As), special events like Savage Love Live, and the Sex & Politics podcast — subscribe here!

First up, passionate sexting with a married man who can’t leave his wife… Michaela has been there, done that:

SINS, I was in a slightly similar situation, except I wasn’t also cheating on my partner as well, which you are doing. I met a great guy and the conversations were the same: Poetic, erotic and something I couldn’t get enough of. Oh, and of course there were a long list of excuses and...

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...heating on my partner as well, which you are doing. I met a great guy and the conversations were the same: Poetic, erotic and something I couldn’t get enough of. Oh, and of course there were a long list of excuses and reasons as to why he couldn’t open his relationship or come clean to his partner. Eventually I found out he was doing the same with multiple people and “making allowances” for himself to get by in a sexless relationship (staying together and staying sane as Dan likes to put it), and I cut him loose. I told him that if he ever leaves or works out ethical non-monogamy to let me know. He isn’t a bad person, just stuck in a shitty situation with dysfunction on both sides of the partnership. Trust me when I say it is not worth the headache. Move on. If SINS wants more than passionate texts and sexts… yeah, she should move on. Her emotional affair partner (EAP) clearly isn’t going to leave his wife, and if that’s what she’s hoping for, she’s going to be disappointed and get hurt. But if SINS is content with the way things are, if passionate texts and sexts are all she really wants or needs, it wouldn’t be irrational for SINS to accept what’s on offer here and resume sexting her EAP. Assuming she can keep her expectations in check — which is easier said than done. Now, it stands to reason that someone who’s cheating on his wife’s with one woman could be doing the same with other women — that shit is a cliché for a reason — but SINS has known her EAP for a long time and may have a better handle on his sincerity than the average affair partner. And, hey, #NotAllMen (and #NotAllWomen) conducting affairs, emotional or otherwise, are guilty of conducting multiple affairs. If the potential emotional fallout of learning her EAP was conducting affairs with other women is too devastating for SINS to contemplate, well, then she should probably end it. (I mean, no one wants to find out a passionate text was copy-and-pasted from some other conversation.) But if the good her’ EAP brings into SINS” life is worth the risk — the risk of there being other women or the risk(s) of the other off-the-shelf bad outcomes an affair might lead to (including discovery, separation, and divorce) — it wouldn’t be nuts for SINS to keep swapping texts and sexts with her EAP. Being a virgin into your mid-twenties? SparkyB has been there, and done that, and had some thoughts to share with the 25-year-old virgin whose letter kicked off this week’s Savage Love: TDG: I know just how you feel. I felt the same way when I was 25. I didn’t have my first kiss until I was 21 and I didn’t have my 2nd kiss, first girlfriend, or first anything else until I was 25 (and I didn’t have a pandemic to blame). I felt exactly as you describe, feeling like I was the only one, that I had missed my chance when I was younger, that no one would want someone at my age as inexperienced as I was. But don’t worry, I’m 40 now and I barely remember what it was like to be the person I was then. My first girlfriend, first time having sex together, etc., wasn’t the end of my insecurity around sex, but slowly I built more experience until I felt like I was having just as satisfying a sex life as my peers. I don’t think I missed too much by starting later, but don’t let that hold you back from starting now if you want to. My first partner was younger than me, but still way more experienced. I don’t think it matters if they’re younger, older, more experienced, equally as inexperienced. All that matters is that they want to be with you and are willing to go at the pace that you need. You don’t have to lead with your inexperience, but do let them know. Don’t be ashamed. And as Dan sometimes says, don’t roll it out like it is cancer. This doesn’t have to be bad news. Can I say — and I’m going to have to say it, because no one else did — that “First Trap” is a pretty good headline for a column about nervously anticipating your first sexual experience. I work hard on my headlines! I recently said that scheduled sex has helped many couples reconnect sexually. Ryan reached out via email to let me know that scheduled sex saved his marriage: I started listening to your podcast about 15 years ago when I found myself in a marriage that was trending towards sexless. I was married to my best friend, but despite her telling me she wanted to have sex with me I couldn’t figure out how to make it happen consistently or successfully. Anyway, rather than asking your advice I just listened to every episode that was available at the time (maybe 100 episodes) and synthesized a plan. First, we had an open and honest conversation about if she wanted to have sex with me – her response was enthusiastic. Second, I had some concerns around hygiene so I proposed that we agree to always shower before intimacy. Third, we agreed to scheduled sex three nights a week at a set time. This allowed her to mentally prepare herself throughout the day so she could be more receptive in the evening and allowed me to not be disappointed on nights we did not have sex. We also had little kids at the time so the scheduling helped us build time into our schedule. Fourth, I couldn’t figure out what turned her on. She had been raised very conservatively and couldn’t communicate to me what she liked, but I knew that occasionally we had great sex, so I knew I was just missing something. Rather than trying to force her to admit something she was very embarrassed about I proposed we google “20 most common kinks” and then just attempt to try all 20 of them. That seemed kind of silly to me, but it worked! Fifteen years later we have a great sex life. I figured out what works for me and what works for her and have come up with some ways to make the two things intersect pretty naturally. Now that our kids are almost grown she wants to explore some more kinky things that are harder to do with kids in the house. It’s pretty great. I am writing this email just to thank you. I don’t know how often people just send you a thank you, but you saved my marriage and kept my family together. I saw someone in your column talk about scheduled sex as a negative and it really bugged me. I came up with that solution on my own (I don’t think you had mentioned it on your podcast as of that time) and it really helped our relationship. I don’t think I’ve ever heard you suggest trying every kink on google to unlock a mega-Christian wife, but maybe that’s a tool you can stick in your mental toolbox! My comments about scheduled sex came in response to a reader who was having an affair with a married man — in the flesh, not on the phone. After five years, TOO cut her affair partner off after he began having “scheduled sex” with his wife, which she described as “consensual rape,” something a lot of commenters took issue with. Well, TOO popped up in the comments herself and responded to my advice. (Which she appreciated — whew!) I’m always happy to see LWs jumping into the comment threads, even when they’re not happy about the advice. In TOO’s case, Ryan, you’ll be happy to know that she walked back her comments about scheduled sex. (Speaking of which: there was an article in the New York Times a few years ago about how couples’ counselors were recommending scheduled sex to their vanilla and monogamous clients — because kinky couples and swinging couples reported having better sex lives and stronger sexual connections with their spouses, and play parties sex and swingers’ events are defined by scheduled sex. So, if it works for the kinky and open, it should work for the vanilla and closed. I’ve tried to find the article without much luck — if anyone’s Google skills are better than mine, or if you remember the story, please drop the link in the comments!) AppleScruff909 had some thoughts about this week’s podcast… Intro: Since when is NRE just a poly thing? And “TikTok stars” is an oxymoron. Caller with chronic pain: Dan’s advice is an option OR you can put it right out there on the table and efficiently weed out the people who can’t handle it, thus preventing you both from wasting “3 or 4 dates” worth of time. (Speaking on behalf of someone with a similar condition.) Dr. Ashley Winter is one of the best guests you’ve had all year. Great answers to great questions! It’s always so great when past callers call back with updates! There have been so many callers over the years that I’ve wished would have given us the epilogues to their stories. NRE — it’s not just a poly thing, but it is a thing poly people named and a thing poly people and very chaotic serial monogamists enjoy more of over the course of their romantic lives than one-and-done types do. Caller with chronic pain: life is short and erring on the side of not wasting other people’s time — and not wasting your own time — is generally good advice. TikTok stars: E!, Out Magazine, Attitude Magazine, Pink News, Gay Times, The Advocate, Yahoo! News — they all described Pierre Boo and Nicky Champa, who have millions of followers on social media, as TikTok stars. Who am I to argue with E!? And finally: Agreed! Dr. Winter is amazing! And more updates from past callers! Please! Another satisfied customer… Hi Dan, you’ve had a profound affect on my life. Around 2011 I saw your “price of admission” video and I had just ended my second marriage, of 14 years. At that time in my life, 1 didn’t really understand how relationships should work. I had always thought that I just needed to find the right person for me, a very self-centered concept. Your advise allowed me to embrace the wonderful things about a partner and forgive the niggles. I have since found my life partner and it’s largely due to your mature words, many years ago. I needed to change, and you were the catalyst. So, thank you and I wish you happiness. That video was recorded many years ago — and many gray hairs ago. I’m glad it helped you. I miss having black hair! I haaaaaaate it when this happens/when I do this: I heard I was mentioned on @fakedansavage recently, and that he said my last name wrong, which is totally common and I’m flattered to be thought of — Elle Stanger, CSE (she/they) (@ElleStanger) July 11, 2023 Sorry, Elle! Stanger! Not Stranger! A caller on Episode 871 wanted to know how to indulge her partner’s vore fetish — people into vore want to be eaten alive and/or swallowed whole — and more than one listener flagged this Instagram post as a possible inspiration for the caller. (It’s a video, but won’t embed here. Click thru to see it in action.) A male caller from this week’s show was shocked when a new partner asked to sound him. (Sounding involves gently sliding a stainless steel and sterilized rod into the urethra.) Most people cringe at the thought — the Tech-Savvy, At-Risk Youth freaked the fuck out — but done correctly, sounding is safe, it isn’t painful, and can be a very sexy and transgressive head trip. My Facebook followers had a few reactions of their own. Ann Marie has had some positive sounding experiences… I have topped using sounds on men and women. They loved it. They did it to themselves in private but loved the drama and spirituality of me doing it to them and my techniques. I personally freak out when I have to be catheterized so it’s not for me. But as a top I found this type of penetration and their responses to it very satisfying. Some white light moments. But Maria doesn’t get it… As a medical professional, this is a horrible idea. I don’t kink shame but this would be a urologist’s nightmare. Terra has some advice… Pro dominatrix here: the majority of my clients who have this kink actually find being on the receiving an incredibly relaxing. However, it is important that you are relaxed and comfortable, as any squirming or movement can cause damage. Also, it’s very important that the woman who wants to sound the caller be experienced and is using professionally-made-medical-grade sounds that were sterilized in an autoclave, wearing gloves, etc., to make sure everything is free of bacteria. While Amy has a devious idea… I’m going to start telling guys this is my kink so they’ll leave me alone. Most guys will leave you alone, Amy. (Hell, the tech-savvy, at-risk youth will run from you.) But some guys — as Terra’s post made clear — would happily pay you for the privilege. And finally: I’ve long described complicated and risky kinks — things like sounding — as “varsity-level kinks.” SloMoPoMo flags a potential problem with that moniker: Just a thought for consideration… does calling it a “varsity-level kink” make it sound attractive to people who would like to think they’re on the varsity team? K2Frank, via Instagram, suggested a great alt: Instead of “varsity-level kink,” maybe “double-black-diamond kink,” like with skiing and snowboarding. Even if you’ve never hit the slopes, “double-black diamond” sounds inherently more intimidating (and caution-inducing) than “varsity level” does. That’s a great suggestion, K2Frank, and I’m going to use it!

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